Реакция #2045002

Уравнение реакции

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl 6-bromohexanoate

→

12

Выход 52.8%

6-{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-hexanoic acid methyl ester

Выход 52.8%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Температураrefluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   ФильтрацияCrude 12 was filtered
5. 5
   Другоеdried
6. 6
   Другоеpurified by column chromatography on silica gel

Методика

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), sodium iodide (2 g, 13.3 mmol) and disodium phosphate (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 6-bromohexanoate (2 g, 9.6 mmol) and refluxed for 24 hours. Acetone was distilled off and water (15 ml) was added. Crude 12 was filtered, dried and purified by column chromatography on silica gel using benzene:ethyl acetate (9:1) to give pure 12 (1.5 g, 52.8%) as a pale white powder. The melting point was found to be 69.2-70.8° C.

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